Water → HCID 14570119, compound

HRID 2354284Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-:17].[K+].[K+].[OH2:22].[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:26]2[CH:27]=[CH:28][C:23]([C:29]([O:17][CH3:16])=[O:22])=[CH:24][CH:25]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)benzoate (1.0 g), 1-benzyloxy-3-iodobenzene (1.18 g), tetrakis(triphenylphosphine)palladium(0) (0.22 g) and potassium carbonate (1.58 g) in toluene (10 mL) was stirred at 100° C. under an argon atmosphere overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethylacetate. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=9/1-4/1) to give methyl 4-[3-(benzyloxy)phenyl]benzoate (1.2 g).

Workup

extractionthe resulting mixture was extracted with ethylacetate
washThe extract was washed with water and brine successively
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=9/1-4/1)

Sources & evidence

ORD record: ord-2616007c37c546b9b3509a191a783f11
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750145B2

Reaction notes

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